Boronic acids are used as intermediates in the synthesis of biaryl and related architectures (Hall, D. G. Ed. Boronic Acids, Wiley-VCH: Weinheim, Germany, 2005), as building blocks for supramolecular polymers (Niu, et al., J. Chem. Commun. 2005, 4342), chemical sensors (James and Shinkai, Top. Curr. Chem. 2002, 218, 159) and therapeutics. The broad applicability of boronic acids in organic synthesis has encouraged pursuit of efficient methods for their synthesis. The traditional approach to arylboronic acids involves the formation of aryl Grignard and lithium reagents, followed by electrophillic trapping with trialkyl borates and subsequent hydrolysis. As it employs the least expensive reagents, this method is one of the few procedures that is used for large-scale applications. The sensitivity of this reaction to moisture and the incompatibility of Grignard and organolithium reagents with electrophillic functional groups are obstacles to its implementation. One solution to this problem is the “in-situ” quench technique, wherein an alkyl lithium reagent is added directly to a solution of aryl halide and trialkyl borate. While this is an improvement, yields are still inadequate for many substrates including carboxylic esters (Li, et al., J. Org. Chem. 2002, 67, 5394). An attractive alternative to direct boronic acid synthesis involves transition metal catalyzed installation of a cyclic boronate ester. The most well known method utilizes Pd(O) (Ishiyama, et al, J. Org. Chem. 1995, 60, 7508; Murata, et al., J. Org. Chem. 1997, 62, 6458) to catalyze the addition of tetraalkoxydiboron (Ishiyama, et al, J. Org. Chem. 1995, 60, 7508; Brotherton, et al., J. Am. Chem. Soc. 1960, 82, 6242; Lawlor, et al., Inorg. Chem. 1998, 37, 5282; Ishiyama, et al., J. Ed. Org. Synth. 2000, 77, 176), pinacolborane (HBPin) (Murata, et al., J. Org. Chem. 1997, 62, 6458; Tucker, et al., J. Org. Chem. 1992, 57, 3482) or catecholborane (Murata, et al., J. Org. Chem. 2000, 65, 164) to an aryl iodide, bromide or triflate. A one-pot Ir catalyzed direct C—H boration was developed to synthesize the relatively inaccessible 3,5-disubstiuted aryl boronic acids and aryltrifluoroborates from 1,3-disubstituted arenes Pd-catalyzed borations of aryl halides and direct Ir catalyzed C—H borations are restrictively expensive due to the cost or extremely difficult synthesis and purification of alkoxydiborons and catalysts (Brotherton, et al., J. Am. Chem. Soc. 1960, 82, 6242; Lawlor, et al., Inorg. Chem. 1998, 37, 5282; Ishiyama, et al., J. Ed. Org. Synth. 2000, 77, 176).
Despite the aforementioned research, there is a need in the art for a simplified, low cost method for the production of biaryl compounds and their boron containing precursors.